Perchlorinated quinones are well known in the art providing a variety of uses in both the chemical and pharmaceutical industries. For example, chloranil (2, 3, 5, 6-tetrachloro-p-benzoquinone) is a powerful oxidant which has been used in the oxidation and dehydrogenation of a large number of organic compounds. It is used commercially as an oxidizing agent in the preparation of dyes such as methyl violet and as a fungicide in agricultural applications. Chloranil is also known to be a useful reagent for tamaquine detection in urine.
Various industrial processes exist for the manufacture of chloranil. U.S. Pat. No. 2,722,537 (Fox) discloses a process for the preparation of chloranil through oxidative chlorination of cyclohexane using hydrogen chloride and oxygen at a temperature between 180.degree. and 260.degree. C. U.S. Pat. No. 2,414,008 (Alquist et. al.) discloses the production of chloranil by admixing a polychlorophenol with concentrated sulfuric acid and passing chlorine into the heated mixture. U.S. Pat. No. 2,422,229 (Fletcher) discloses a process for manufacturing chlorinated quinones by chlorination of derivatives of phenol and alphahydroxynapthalene, the derivatives being present in a liquid medium comprising a mixture of sulfuric acid and acetic acid.
Although the above noted prior art processes do in fact produce chloranil, they often suffer from low yields and exist as relatively "dirty" reactions generating excessive and unwanted byproducts.